Acetic Anhydride → Ammonia methanol dichloromethane

HRID 2404458Notes

Reaction equation

HRID 2404458 reaction equation
[ClH:1].[ClH:2].[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH:12]([O:26][CH:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1)[C:13]1[CH:14]=[C:15]([S:19][CH2:20][CH2:21][NH:22][C:23]([NH2:25])=[NH:24])[CH:16]=[CH:17][CH:18]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>C(#N)C.CN(C)C1C=CN=CC=1>[Cl:1][CH2:4][Cl:2].[CH3:12][OH:26].[NH3:3].[C:34]([NH:24][C:23]([NH:22][CH2:21][CH2:20][S:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH:12]([C:4]2[NH:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:3]=2)[O:26][CH:27]2[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]2)[CH:14]=1)=[NH:25])(=[O:36])[CH3:35]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 178480514HCID 178480514, compound

Product 2

HCID 21584172Ammonia methanol dichloromethaneHCID 178475105HCID 178475105, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(2-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)-methyl]phenylsulfanyl}ethyl)guanidine.dihydrochloride (100 mg) in dry acetonitrile (1 mL) is added acetic anhydride (64 mg) et 4-dimethylaminopyridine (51 mg). After 24 hours at room temperature, solvent and volatiles are removed under reduced pressure. The residue is purified by chromatography (toluene/acetone/triethylamine 50/50/1 then gradient dichloromethane/methanol/ammonia from 95/5/0.5 to 90/10/1) to give N-acetyl-N′-(2-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}ethyl)guanidine.

Workup

  1. customsolvent and volatiles are removed under reduced pressure
  2. customThe residue is purified by chromatography (toluene/acetone/triethylamine 50/50/1

Sources & evidence

ORD record
ord-c3ab9301ce3a4451b51814c208a8678b
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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